WO2004111063A3 - Chiral ligands for application in asymmetric syntheses - Google Patents

Chiral ligands for application in asymmetric syntheses Download PDF

Info

Publication number
WO2004111063A3
WO2004111063A3 PCT/EP2004/005930 EP2004005930W WO2004111063A3 WO 2004111063 A3 WO2004111063 A3 WO 2004111063A3 EP 2004005930 W EP2004005930 W EP 2004005930W WO 2004111063 A3 WO2004111063 A3 WO 2004111063A3
Authority
WO
WIPO (PCT)
Prior art keywords
application
asymmetric syntheses
chiral ligands
syntheses
asymmetric
Prior art date
Application number
PCT/EP2004/005930
Other languages
German (de)
French (fr)
Other versions
WO2004111063A2 (en
Inventor
Benjamin Meseguer
Dieter Arlt
Original Assignee
Bayer Chemicals Ag
Benjamin Meseguer
Dieter Arlt
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2003127109 external-priority patent/DE10327109A1/en
Priority claimed from DE2003137013 external-priority patent/DE10337013A1/en
Application filed by Bayer Chemicals Ag, Benjamin Meseguer, Dieter Arlt filed Critical Bayer Chemicals Ag
Priority to JP2006515817A priority Critical patent/JP5009613B2/en
Priority to EP04739512.4A priority patent/EP1636243B1/en
Priority to US10/571,722 priority patent/US7396947B2/en
Priority to ES04739512.4T priority patent/ES2443994T3/en
Publication of WO2004111063A2 publication Critical patent/WO2004111063A2/en
Publication of WO2004111063A3 publication Critical patent/WO2004111063A3/en
Priority to US11/298,641 priority patent/US20060161022A1/en

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C07F15/0053—Ruthenium compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5027—Polyphosphines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5329—Polyphosphine oxides or thioxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65525—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a seven-(or more) membered ring
    • C07F9/65527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a seven-(or more) membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium

Abstract

The invention relates to biarylbisphosphines and intermediates thereof. Furthermore, the invention relates to catalysts produced from the biarylbisphosphines and the use thereof in asymmetric syntheses.
PCT/EP2004/005930 2003-06-13 2004-06-02 Chiral ligands for application in asymmetric syntheses WO2004111063A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2006515817A JP5009613B2 (en) 2003-06-13 2004-06-02 Chiral ligands for use in asymmetric synthesis
EP04739512.4A EP1636243B1 (en) 2003-06-13 2004-06-02 Chiral ligands for application in asymmetric syntheses
US10/571,722 US7396947B2 (en) 2003-06-13 2004-06-02 Chiral ligands for application in asymmetric syntheses
ES04739512.4T ES2443994T3 (en) 2003-06-13 2004-06-02 Chiral ligands for use in asymmetric synthesis
US11/298,641 US20060161022A1 (en) 2003-06-13 2005-12-08 Chiral ligands for application in asymmetric syntheses

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE10327109.0 2003-06-13
DE2003127109 DE10327109A1 (en) 2003-06-13 2003-06-13 Novel intermediates and dichloro-biarylbisphosphines are useful as ligands for transition metal complex catalysts used in the production of enantiomer-enriched compounds
DE2003137013 DE10337013A1 (en) 2003-08-12 2003-08-12 New bisarylbisphosphine compounds are used for production of catalysts for asymmetric synthesis
DE10337013.7 2003-08-12

Publications (2)

Publication Number Publication Date
WO2004111063A2 WO2004111063A2 (en) 2004-12-23
WO2004111063A3 true WO2004111063A3 (en) 2005-03-31

Family

ID=33553457

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2004/005930 WO2004111063A2 (en) 2003-06-13 2004-06-02 Chiral ligands for application in asymmetric syntheses

Country Status (5)

Country Link
US (2) US7396947B2 (en)
EP (1) EP1636243B1 (en)
JP (1) JP5009613B2 (en)
ES (1) ES2443994T3 (en)
WO (1) WO2004111063A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4905917B2 (en) * 2005-12-27 2012-03-28 株式会社ダイセル Production method of vinyl ether compounds
CN110494439B (en) * 2017-04-11 2022-11-08 帝斯曼知识产权资产管理有限公司 Chiral biphenyl diphosphine ligand and preparation method thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001021625A1 (en) * 1999-09-20 2001-03-29 The Penn State Research Foundation Chiral phosphines, transition metal complexes thereof and uses thereof in asymmetric reactions
EP1095946A1 (en) * 1999-10-29 2001-05-02 Takasago International Corporation Optically active diphosphine compound, production intermediates therefor, transition metal complex containing the compound as ligand and asymmetric hydrogenation catalyst containing the complex
EP1186609A2 (en) * 2000-09-11 2002-03-13 Bayer Ag Diphosphines
US20020128501A1 (en) * 2000-11-17 2002-09-12 The Penn State Research Foundation Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catalytic reactions

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK0398132T3 (en) 1989-05-18 1995-12-18 Hoffmann La Roche phosphorus compounds
DE19522293A1 (en) * 1995-06-20 1997-01-02 Bayer Ag New bisphospins as catalysts for asymmetric reactions
US6162929A (en) 1997-12-23 2000-12-19 Hoffmann-La Roche Inc. Process for the manufacture of bisphosphine oxide and bisphosphonate compounds
JP3549390B2 (en) 1998-03-23 2004-08-04 高砂香料工業株式会社 Ruthenium-phosphine complex and method for producing the same
JP3146187B2 (en) * 1998-06-26 2001-03-12 高砂香料工業株式会社 Novel method for producing diphosphine oxide
US6288280B1 (en) * 1999-07-09 2001-09-11 Hoffmann-La Roche Inc. Racemization of atropisomeric bis(phosphine oxide) compounds
IT1313897B1 (en) 1999-10-25 2002-09-26 Fata Group S P A AUTOMATED IMPROVED STATION FOR ASSEMBLING AND WELDING OF VEHICLE BODIES
EP1257360A4 (en) * 2000-02-10 2003-08-27 Penn State Res Found Chiral ferrocene phosphines and their use in asymmetric catalytic reactions
DE10027154A1 (en) * 2000-05-31 2001-12-13 Bayer Ag Process for the production of optically active trimethyllactic acid and its esters
US6480513B1 (en) * 2000-10-03 2002-11-12 K2 Optronics, Inc. Tunable external cavity laser
US6476235B2 (en) * 2001-01-09 2002-11-05 Warner-Lambert Company Process for the synthesis of 5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide
US6743921B2 (en) * 2002-01-24 2004-06-01 Dsm Catalytica Pharmaceuticals, Inc. Process for the preparation of nonracemic syn-1-(4-hydroxy-phenyl)-2-(4-hydroxy-4-phenyl-piperidin-1-yl)-1-propanol compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001021625A1 (en) * 1999-09-20 2001-03-29 The Penn State Research Foundation Chiral phosphines, transition metal complexes thereof and uses thereof in asymmetric reactions
EP1095946A1 (en) * 1999-10-29 2001-05-02 Takasago International Corporation Optically active diphosphine compound, production intermediates therefor, transition metal complex containing the compound as ligand and asymmetric hydrogenation catalyst containing the complex
EP1186609A2 (en) * 2000-09-11 2002-03-13 Bayer Ag Diphosphines
US20020128501A1 (en) * 2000-11-17 2002-09-12 The Penn State Research Foundation Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catalytic reactions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ZHANG Z ET AL: "Synthesis of chiral bisphosphines with tunable bite angles and their applications in asymmetric hydrogenation of beta-ketoesters", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 65, no. 19, 19 August 2000 (2000-08-19), pages 6223 - 6226, XP002214812, ISSN: 0022-3263 *

Also Published As

Publication number Publication date
US20060161022A1 (en) 2006-07-20
ES2443994T3 (en) 2014-02-21
EP1636243B1 (en) 2013-11-06
JP5009613B2 (en) 2012-08-22
WO2004111063A2 (en) 2004-12-23
EP1636243A2 (en) 2006-03-22
JP2006527221A (en) 2006-11-30
US20070004927A1 (en) 2007-01-04
US7396947B2 (en) 2008-07-08

Similar Documents

Publication Publication Date Title
AP2005003470A0 (en) Novel peptides that bind to the erythropoietin.
WO2004099249A3 (en) Optimized fc variants and methods for their generation
IL173589A0 (en) Trans-1 (6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine
AP2005003426A0 (en) Cannabinoid receptor ligands and uses thereof.
AP2005003427A0 (en) Cannabinoid receptor ligands and uses thereof.
AP2005003466A0 (en) Cannabinoid receptor ligands and uses thereof.
AP2006003562A0 (en) Antibodies to M-CSF.
EP1954703A4 (en) Novel dinuclear transition metal compound, catalyst composition comprising the same, method of preparing olefin polymer, and olefin polymer produced using the method
NL1028877A1 (en) Catalysts.
WO2005047545A3 (en) Microarray controls
GB0305175D0 (en) Navigator 2.0 features
IL187006A0 (en) Ferrocenyl ligands, production and use thereof
IL175138A0 (en) Tetrafluorosegphos, asymmetric hydrogenation
EP1695761A4 (en) Catalyst composition
GB2409684B (en) Liquid medium, its use and methods for its production
ZA200306777B (en) Fische-Tropsch catalyst regeneration.
WO2005047299A3 (en) Chiral di- and triphosphites
AU2003225962A1 (en) Phosphinometallocenylamides as novel ligands for asymmetric catalysis
WO2004111063A3 (en) Chiral ligands for application in asymmetric syntheses
EP1723125A4 (en) Novel 1,2,4-benzotriazine-1,4-dioxides
ZA200400680B (en) Distillation method.
WO2004104014A3 (en) Chiral ligands and their transition metal complexes
AU2003205736A1 (en) Pyrimidinonesulfamoylureas as integrin ligands
WO2004075028A3 (en) Systems and methods for variable rebate and incentive programs
PL1747205T3 (en) Chiral phosphine ligands, their preparation, catalysts thereof and their use

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2004739512

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 11298641

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 2006515817

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 2007004927

Country of ref document: US

Ref document number: 10571722

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 2004739512

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 10571722

Country of ref document: US